Aug. 31, 2020

Showdown at the Ikedaya Inn: Samurai Secret Police

Showdown at the Ikedaya Inn: Samurai Secret Police

On June 5th, 1864, the Shogun’s secret police raced against time to foil a sweeping terrorist plot in Kyoto. The ensuing bloodbath would have far-reaching consequences for the future of Japan.

On June 5th, 1864, the Shogun’s secret police raced against time to foil a sweeping terrorist plot in Kyoto. The ensuing bloodbath would have far-reaching consequences for the future of Japan



Hillsborough, Romulus. Shinsengumi: The Shogun’s Last Samurai Corps. 2005.

Hillsborough, Romulus. Samurai Revolution. 2014. 

Hillsborough, Romulus. Samurai Assassins. 2017. 

Jansen, Marius B. The Making of Modern Japan. 2000.

Ravina, Mark. The Last Samurai: The Life and Battles of Saigo Takamori. 2004.

Esposito, Gabriele. Japanese Armies, 1868-1877. 2020.

Charles Rivers Editors. Commodore Matthew Perry. 2020. 


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When the sun rose over the city of Kyoto, Japan on June 5th, 1864, Kotaka Shuntaro had been hanging by his feet for hours.


He was still alive. Barely.


His back had been shredded by whips. His limbs had been beaten til they were purple. His breathing was ragged and strained. All of this torture was part of a pitiless interrogation that had lasted almost 8 hours.


And all Kotaka had to do to make it stop, was give his captors the information they wanted. His silence, they assured him, was slowly killing him.


Throughout the night, they had asked him lots of questions. Over and over again. But Kotaka wouldn’t say a word. According to an eyewitness, the prisoner “closed his eyes, clenched his teeth, and passed out, but he would not open his mouth.”


8 hours earlier, Kotaka has been asleep in his bed. He owned a small shop in the mercantile district of Kyoto, and he was exhausted after a long day of running the store. But in the middle of the night, he was awoken by a noise. The sound of someone walking up the steps to his bedroom.


Before he could even get up, the door to his room slid open, and Kotaka saw several silhouettes step in to the cramped room.  He could see that all of these men were heavily armed. They each wore two swords on their hip, a long one and a short one. Kotaka knew what that meant. That meant that these men were samurai.


But why were they at his house in the middle of the night? It became painfully clear when one of the swordsmen spoke out from the gloom: “By the authority of the protector of Kyoto, you are under arrest, for conspiring to overthrow the government.”


Kotaka’s heart sank. They must know everything, he thought. And sure enough, these midnight visitors knew a lot about Kotaka. The humble shopkeeper was not just any old shopkeeper. In fact, he was a key conspirator in an imminent act of domestic terrorism.


The evidence of his guilt had been found in a secret compartment in the walls of his shop by these midnight visitors.


They found a huge cache of guns, powder, and ammunition. An entire arsenal.


This evidence was damning enough. But something else was found in the walls of Kotaka’s shop. A small written document. A terrorist manifesto that spelled out in no uncertain terms what was about to happen in the sleepy city of Kyoto.


The terrorists, whoever they were, were planning to take aim at the highest authority in the country. None other than the Emperor of Japan, who lived in his opulent palace at the center of the city. The plan was simple. The conspirators would assassinate a number of key city administrators, kidnap the Emperor, and start a fire that would burn the city to the ground.


As Kotaka hung upside down from the rafters at a black site somewhere in Kyoto, he was determined not to give up his compatriots. No matter what these men did to him, he would not talk. If he kept his mouth shut, then they plan might still have a slim chance of success. His captors knew the broad details of the plot, but they didn’t know when, or who, or how.


If Kotaka could just endure the excruciating pain and stay silent, within 24 hours, Kyoto would be a pile of ash, and the Emperor himself would be on a ship bound for the southern reaches of Japan. Far away from these brutal samurai who were taking the skin off his back piece by piece.


On June 5th, 1864, the clock was ticking.




It was a clock that had started ticking almost a decade earlier, on the other side of the Pacific Ocean. In Norfolk, Virginia, of all places.


On the chilly morning of November 24th, 1852 four ships steamed out of Norfolk harbor. Their commander was a Senior Naval officer named Matthew Perry. Commodore Matthew Perry. As the Commodore strode the deck of his flagship that morning, his thoughts must’ve been constantly circling back to the letter he had locked away in his quarters.


It was a letter signed and sealed by the President of the United States, Millard Fillmore himself. Commodore Perry had been tasked with taking that letter, and his four ships, almost 3,000 miles to the west. Across the vast expanse of the Pacific Ocean to a mountainous island chain off the coast of mainland Asia.


To Japan.



In the mid-19th century, the world was rapidly changing.


Widespread industrialization and meteoric technological advances had catapulted the seafaring capabilities of Western nations into the stratosphere. Ships could go farther, faster, and with greater confidence.


As a result, the map was shrinking extremely fast. Imperialism was in full swing. And everyone, from Great Britain, to Russia, to Belgium wanted their piece of the pie. Places like Africa and India and China were money trees just waiting to be harvested. The trade opportunities and resource deposits in these exotic locales were almost limitless. This was a game of Hungry Hungry Hippos on a global scale; you had to act fast if you wanted to walk away with a prize.


And few nations were hungrier to carve out some of this prosperity than the United States of America.


By this point the notion of Manifest Destiny had really taken hold in the national consciousness. Expand, expand, expand. After conquering the American West, if not fully taming it, the US began looking beyond the golden shores of California, in a desire to project its power and influence into East Asia.


In preparation for his mission, Commodore Matthew Perry had read as many books about Japan as he could get his hands on. But honestly, there wasn’t much available. There were a few thin translations from old Dutch sources.  Scattered accounts from traders and Jesuit missionaries. But to the Western world, Japan was still more-or-less a complete mystery.


And Commodore Matthew Perry was determined to unravel it.


Truth be told, Perry had not wanted this assignment at all. He’d been promised a cushy gig pursuing US interests in the Mediterranean. He’d pictured himself getting a bronze tan and sipping strong wine on the sunny shores of old Europe. As he complained:


“I confess that it will, to me, be a serious disappointment, and cause of personal inconvenience not to go to the Mediterranean, as I was led to believe.”


Instead, he was being sent to a cold, rainy, jagged island chain on the edge of the map. But Perry was an optimist, if nothing else. There had to be some glory buried in this unglamorous assignment.


Perry and his men would’ve been more than a little apprehensive as their ships steamed across the Pacific, closer and closer to Japan. The last time a foreign power had tried to strong-arm its way into Japan, it had been soundly repelled. The Mongol Empire had tried, and failed, twice to conquer the Japanese home islands. Even Kublai Khan himself couldn’t manage to bend this scrappy archipelago to his will.


But Commodore Perry knew there was more than one way to skin a cat. He had at his disposal, the awesome power and resources of the burgeoning American empire, and a mandate from the President himself to use those resources. This was a nut that could be cracked. Had to be cracked.


But what were Commodore Perry and his men walking into? What was Japan like in the year 1853? Well the truth was, Japan in 1853, was not all that different from Japan had in 1653.


For 250 years, Japan had been closed off from the rest of the world. After centuries of civil war and cyclical violence, the country had finally been united under a single powerful warlord, called the Shogun. That title, “Shogun”, essentially just means “generalissimo”, or “commander-in-chief.” After uniting Japan under a single government, the Shogun and his descendants had made the decision to cut Japan off from the outside world.


No one in, and no one out.


In modern times, especially in the West, we take the basic concept of international travel for granted. We can leave our home country, go to others, come back, go to a different one. Well, this was not possible in pre-modern Japan. In fact, it was explicitly forbidden by law.


There were no passports. No VISAs. If you left Japan, you would not be allowed back in. In fact, if you were foolish enough to actually return after leaving the country, you would likely be put to death. And this extended to a domestic travel ban as well for the lower classes; if you so much as left the province where you were born, you could be punished.


But the main purpose of all of these restrictions, was that the Shogun didn’t want outsiders coming into Japan.


European ships were banned from all but one harbor. In fact, foreign vessels could be attacked and sunk on sight with zero repercussions. This was known as the “Don’t Think Twice” Decree. The Shogunate – the military government -  did not want outside ideas, thoughts, or religions polluting the peaceful society they had worked so hard to cultivate.


As the Shogun decreed:


All Barbarians and Westerners […] worship Christianity, that wicked cult prohibited in our land. Henceforth, whenever a foreign ship is sighted approaching any point on our coast, all persons on hand should fire on and drive it off. When in doubt, drive the ship away without hesitation.”


No one in. No one out.


All of this led to societal and technological stagnation. It was like time itself had been frozen. And for 250 years, the Japanese lived, worked, died, and governed much as they had in the year 1600. As historian Marius B. Jansen wrote, Japan was “a cocoon, seldom penetrated from without.”


But the American ships that entered Japanese waters on July 8th, 1853 were not the kind that could be casually driven away.  They were unlike any vessels the Japanese had ever seen. These ships were huge. Six times the size of anything that existed in the Eastern hemisphere. They were plated in black iron. They belched clouds of smoke and steam. They were bristling with cannons and guns that could rain down destruction from a mile away.


When he saw these things, the Japanese harbormaster noted with alarm:


They can move about freely without the use of sail or oar, and can come and go with great speed. They are just like floating castles which can move about as they please.


After six months, Commodore Matthew Perry had arrived at his destination. As a Japanese official remembered bitterly years later:


When the American barbarians arrived, although they knew that it was prohibited by law, they came into the harbor, gave us white flags as a symbol of peace, presented their letter, then proceeded further into the bay. They fired blank shots from their cannons, and even took soundings as they wished. Their arrogant insult was … truly the worst humiliation in the history of our country…. They continued to violate our laws and moved further into the bay close to the castle, threatening us and making demands upon us.”


As historian Romulus Hillsborough writes:


“For the first time in history, foreign warships threatened the shōgun’s capital.”


After this show of force, Commodore Perry and his men splashed ashore and presented Millard Fillmore’s letter to the hastily assembled Japanese delegation. It said that the President hoped:


“That the United States and Japan should live in friendship and have commercial intercourse with each other.”


But the truth was, this was not a request. And the Japanese knew it. They had heard what had happened to China when Europe came calling at their ports. How Britain, France, Russia and others had kicked down the door to that ancient country. How the Chinese been forced to sign unfair trade deals and exploitive treaties. How opium had flooded the country and ruined millions of lives. One Japanese politician remarked at the time:


“It is deplorable to think that the refined culture of China might be transformed into a filthy European world,”


The Japanese knew all to well what they were in for if the Americans were allowed to enter the country. As one lord prophesized:


“The foreign barbarians will propagate Christianity to trick the people of our sacred land, conduct trade with us, pillaging our wealth, impoverishing our people, and finally taking our country through military force.”


As news spread throughout Japan about this swaggering American sailor and his “black ships” – as they were called – all eyes turned to Japan’s military leader, the Shogun, to defend the country. If anyone could throw these arrogant imperialists back into the sea, it was the most powerful warlord in the land. Right?


Well the Shogun, to put it politely, was not up to the task.


Since the country had been united 250 years before, thirteen men had held the mantle of Shogun. What began as a title that had to be earned through strength, intelligence, and political cunning, evolved into a toothless hereditary position. Shoguns were born not made; appointed to the position based purely on their genealogy, regardless of merit or competence.


Anyone who’s studied the general trend of monarchies knows that this a foolproof recipe for weak, ineffectual leaders. The Shogun who found himself facing the arrival of the Americans was no exception. As Romulus Hillsborough describes in his book, Samurai Revolution, the Shogun was:


“sickly, suffered a speech impediment, and was unable to sit upright for extended periods of time—after about thirty minutes his body would tremble and he would become prone to convulsions. He was introverted, had no interest in women, and shied away from all but his closest relatives and attendants. One writer reports that the supreme leader of Japan’s military government was unable to stand up on his own to urinate—so that each time he went to the latrine he needed an attendant to help him.”


But even for a strong, competent leader, the looming political choice would have been an agonizing one. Romulus Hillsborough goes on:


“The Shogunate […] found itself faced with the greatest dilemma in its history. Yielding to the American demands for a treaty would make Japan seem weak, which, in turn, might invite foreign aggression. But rejection might incite war, which the Shogunate had no hope of winning.”


The people of Japan became deeply polarized on the issue of how to respond to these foreign visitors. Two factions emerged, with two slogans. “Expel the barbarians” on one side, and “Open the country” on the other. The hawks and the doves. The hawk argument was simple. One prominent samurai lord said at the time:


“If we put our trust in war, the whole country's morale will be increased and even if we sustain an initial defeat we will in the end expel the foreigners; while if we put our trust in peace, even though things may seem tranquil for a time, the morale of the country will be greatly lowered and we will come in the end to complete collapse.”


In a nutshell, if we let these outsiders end, they will bleed us dry. They will infiltrate our country and take advantage of us. We all know what happened to China. We know what happened to India. We cannot allow ourselves to become a territory of some Western power to be abused and exploited. We have to fight back. We have to at least try, even if it ends in defeat.


The consequences of opening the country, it was believed, would be cultural devastation.


As one diplomat urged:


“There are, moreover, many curiosities and concoctions from abroad that dazzle the eyes and entice our people to glorify foreign ways. Should the wily barbarians someday be tempted to take advantage of this situation and entice our stupid commoners to adopt beliefs and customs that reek of barbarism, how could we stop them?


The other side of the debate, the “Open the country” doves, argued that resistance would be futile and ultimately disastrous. One politician said:


“... it is impossible in the crisis we now face to ensure the safety and tranquility of our country merely by an insistence on the seclusion laws as we did in former times.”


Basically, there was no getting the toothpaste back inside the tube now. The world had changed. The fragile cocoon of isolation that the Shoguns had carefully cultivated for two and half centuries centuries was officially punctured. Japan had to adapt or die.


The “Open the country” faction argued, “look guys, we don’t want to make a deal with the Americans any more than you do, but we don’t have the means of fighting back. We’re not strong enough to resist their technology and firepower. We have bows and swords. They have guns and cannons. ….But -  if we can bide our time, and learn how to use their technology, modernize, eventually we could fight back.


As on prominent samurai lord said:


“To control the barbarians, we must know the barbarians.  We must control the barbarians through barbarian technology,”


Many agreed with this pragmatic approach, arguing:


“Fighting [the foreigners] and being defeated, and [as a result] having our country rent asunder, would bring the worst possible disgrace upon our nation. Our only choice for the time being is to concede [to a treaty], as the lesser of two evils.”


This debate raged back and forth for months. But eventually the Shogunate made up its mind. One Japanese politician remembered years later:


“At that time the Shogunate decided to open the country, and gradually did so. There were many people, including feudal lords, who resented this. They said that the Shogunate was forced by the barbarians to open the country because of its cowardice and weakness, and that this was why the Shogunate submitted to this humiliation. They no longer believed in the Shogun. There was heated argument everywhere.”


On July 29th, 1858 , a trade deal was signed with America. After that it was open season. Trade deals were signed with Great Britain. Then France. Then Russia. The dominos fell rapidly, and in a matter of months, foreigners were flooding into Japan, bringing with them new languages, new fashions, new weapons and new ideas.


The hawks were horrified. Two centuries of carefully cultivated isolation…overturned almost overnight.


But they would not go down without a fight. With the advent of this humiliating treaty, the seeds had been planted for a fanatical nationalist insurgency. A wave of coordinated domestic terrorism that would sooner see Japan burned to the ground than submit to outside influences.


The ink on the treaties may have been dry, but the blood was just beginning to flow.


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On March 3, 1860, two years after the Shogunate had signed its extremely controversial trade deal with the United States, it was snowing in the capital city of Edo. A person who was there that day remembered:


The snow-flakes fell so thickly that objects only a few yards away could not be distinctly seen.”


As the spring snows covered the rooftops, a very important man was making his way through the city streets, surrounded by an entourage of sixty armed guards.


This man was the Shogun’s Regent, a guy named Ii Naosuke. (don’t worry, you don’t need to remember that).  Second only to the Shogun, he was the most powerful politician in Japan. If you were looking for the man in charge, this was the guy. In fact, Naosuke had personally negotiated, drafted, approved, and signed the treaty with the United States.


A crowd had gathered to watch his procession as it moved through the capital. Merchants and street vendors sold hot tea and sake in the cold as the famous politician rode past.


But mingling amongst the crowd, blending in with the ordinary merchants and townspeople, were 18 ronin – or rogue samurai. They were disguised as ordinary peasants, wearing wide brimmed hats and red lacquered raincoats. But under those red raincoats, each of them carried a weapon. Razor-sharp swords intended for a very specific purpose.


Earlier that day, all 18 of these ronin had signed their names to a written document. A manifesto. They wanted all of Japan to understand their reasons for what they were about to do. Like many in the country, they were angry that this man, the Shogun’s regent, had allowed:


“Foreigners to build places of worship for their evil religion. This wicked man has proved himself an unpardonable enemy of this nation. It is our duty to put an end to this serious evil. To be the instruments of heaven.”


As the Regent and his entourage passed the threshold of a castle gate, the assassins struck. One of the disguised ronin fired a pistol into the air. That was the signal to attack.


All 18 ronin throw off their raincoats, draw their swords, and rush the procession They begin hacking the Regent’s bodyguards to death in broad daylight. According to Hillsborough,


One of the assassins tore open the door, grabbed Ii Naosuké by the back of the neck, and pulled him out. He struck the regent with his sword on the top of the head; and as Ii fell forward and tried to get up, the assassin beheaded him. With the head skewered on the tip of his sword, he held the trophy up high and triumphantly announced that he’d killed the regent. The assassins then fled, their objective accomplished in just a matter of minutes.”


There’s actually a very famous woodblock painting of this ambush, and it does an amazing job of showing just how chaotic this attack was. It was fast, dirty, and bloody. In the painting, you can see what looks like a pitched battle in the middle of a city street. There’s blood spattered all over the snow, the ronin are swinging their swords and chopping limbs off. You can see men biting off fingers and stabbing each other. And in the center is the Regent, in his palanquin or carriage, seconds away from being killed and decapitated.


All of this lasted less than 15 minutes. In a single terrorist attack, Japan had been turned completely upside down. As one historian wrote:


The assassination of Ii Naosuké was the most important event of the era. It brought a sea of change to the political and cultural landscape of the country. […]


If the most powerful man in Edo could be cut down by a small band of assassins, there was no limit to the havoc that hundreds, or even thousands, of rōnin could wreak throughout Japan.


These 18 ronin were just a tiny fraction of a much larger ideological movement. Thousands of like-minded warriors felt betrayed by the Shogunate and wanted to see its government toppled by any means necessary.  


As shocking as this murder was, it was only the beginning of a widespread terror campaign that would completely engulf the country. And Shogunate officials were not the only ones who found themselves falling under the blades of these fanatical rogue samurai.


The ronin also targeted foreigners – Westerners, Europeans, and Americans. Their hatred and xenophobia was extremely intense. As one historian wrote, to many Japanese:


“Foreigners were monsters with long noses, round eyes, and red or yellow hair, who partook of human flesh and who harbored unholy designs on the sacred empire.”


To these ronin, even foreign languages and writing were obscene and filthy:


“The shapes of foreign letters are confused and irregular, wriggling like snakes or larvae of mosquitos. The straight ones are like dog's teeth, the round ones are like worms. The crooked ones are like the fore legs of a mantis, the stretched ones are like slime lines left by snails. They resemble dried bones or decaying skulls, rotten bellies of dead snakes or parched vipers.”


Three months after the assassination of the Regent, two Russian sailors were brutally murdered in the port city of Yokohama. The Russians were:


“left in a pool of blood, the flesh hanging in large masses from their bodies and limbs. The sailor was cleft through his skull to the nostrils, half the scalp sliced down and one arm nearly severed from the shoulder through the joint. The officer was equally mangled, his lungs protruding from a sabre gash across the body; the thighs and legs deeply gashed.


The ferocity of the attack deeply unnerved the international community, as a British foreign official observed:


“The manner in which the murdered men were slashed and nearly dismembered, indicated more than a mere desire to disable or kill. There was something savage and vindictive, indicating personal or political feeling, in the number and nature of the wounds. The assassins were not content with simply killing, but must have taken pleasure in cutting them to pieces.”


In the following months, foreigners start getting murdered all over Japan.


A few months after the Russians are killed, a French interpreter was murdered by the ronin. The following month, two Dutch merchants were cut down in middle of the street. Shortly after, two British soldiers are stabbed to death in the middle of the night.


Each time, the killers melted away as quickly as they had appeared. Some were tracked down and captured, but most of these assassins, as Hillsborough writes, “instantly fled and easily escaped in the dark streets.”


As random and vicious as all this violence seemed, there was a rhyme and a reason to these attacks on foreigners.


The ronin believed that by killing Westerners, they could undermine confidence in the Shogunate’s ability to protect foreign diplomats on Japanese soil. They wanted to sabotage the relationship between the Shogun and the Western powers. Essentially, they wanted to trigger a war. One that they hoped would result in the expulsion of the foreign “barbarians”.


But there was another critically important dimension to the “Expel the Barbarians” movement. And it’s a detail that I’ve been holding off on examining until now, because I realize I’m throwing a lot of new information at you. But before we can progress in the story, we need to understand this next bit.  


So we’ve talked about how during this time, Japan was ruled by the Shogun and his government. But technically, the Shogun had a boss.


The Shogun, technically, was just a servant to the Emperor of Japan.


The cultural tradition of an Emperor was over 1,000 years old in Japan at this time. It was one of the few reliable constants in their society. Most Japanese people took it for a granted, indisputable fact that the Emperor was a divine being, part of a bloodline that stretched back all the way to the mythical creation of Japan by the Goddess of the Sun.


With that kind of pedigree, you’d think the Emperor would be the man to talk to for all things political in Japan. Well, that wasn’t really the case. The Emperor’s influence and power had slowly eroded over time, and the Shogunate -  the military government – was the actual shot caller in Japan. The Emperor was still revered as a living god, but the day-to-day running of the country was considered beneath his divine intellect.


Well, these ronin who were terrorizing the country, start to build a cult of personality around the Emperor, and a radical idea takes hold. The Shogun, once so respected and feared, had revealed himself as weak. As it turned out, the commander-in-chief could not protect the country from outsiders. When your top military commander can’t even drive away a small fleet of ships, maybe it’s time for a change.


It was clear that the Shogun could not protect Japan, but maybe the Emperor could. Maybe it was time for the living God to take control of the country and lead Japan into a new era of prosperity and autonomy? As historian Mark Ravina writes in his book The Making of Modern Japan:


A significant and growing number of samurai and commoners throughout Japan were enthralled by the notion that devotion to the emperor could solve the nation's political problems. Central to radical loyalism was the belief that foreigners in Japan constituted a pollution of the "land of the gods" Only by expelling the foreigners could imperial subjects jects prove their loyalty; anything less was not just cowardice, but also a disgrace grace to the emperor and the gods.”


So as the 1860s progress, the country becomes starkly divided between two schools of thought. Those who want to preserve the Shogunate and continue opening the country to Western ideas and influence. And those who want to destroy the Shogunate, elevate the Emperor to his former level of power, and expel the Westerners.


Now because was Emperor was based in Kyoto, that city becomes ground zero for political unrest and factional violence.


The ronin start flocking to Kyoto by the hundreds in a show of support for the Emperor and disapproval of the Shogun. These ronin were restless, violent zealots, looking for any excuse to use the two swords on their hips. Kyoto essentially descends into hotbed of gang warfare, and these ronin with itchy-sword hands begin roaming the streets day and night looking for people to kill.


Almost every morning, Kyoto city workers would find severed heads impaled on bamboo spikes at the city gates. Victims of the ronin.


But the Shogunate, down, out and embattles, had one last ace up its sleeve.


The military government had accumulated massive amounts of wealth over the previous two centuries. And they could use those deep pockets to find some killers of their own. Mercenary samurai who could form a counterterrorist task force and take the fight directly to the fanatical ronin prowling the streets of Kyoto.


The man they turned to was a 29-year-old teacher named Kondo Isami. Now take a second and commit that name to memory, Kondo, K-O-N-D-O. Because Kondo Isami is going to be arguably the most important character in our story moving forward.


As I said, Kondo was a teacher. An instructor, to be specific. But he didn’t teach poetry, or economics, or history. He taught swordsmanship. In essence, he taught people how to kill.


He’d been studying the art of swordplay for about 14 years, almost half his life, but up until that point, he’d never actually killed anyone.


This was actually a big source of personal frustration for many samurai during the pre-modern era. When the OG Shogun had united Japan a couple centuries earlier, he’d put an end to all the cyclical battles and territorial scraps. Almost overnight, the samurai became warriors without a war to fight. For most of them, the swords on their hip were ceremonial. They could use them in a practice dojo, but when it came to actually sticking that cold steel into a warm human body, many 19th century samurai were useless.


As one reformer named Katsu Kaishu explained:


During the more than two hundred years of peace [the samurai] indulged in luxury, lapsed into idleness, and eventually became soft.”


Well, Kondo Isami was not soft.


He did know how to use his sword. He had an encyclopedic knowledge of technique and theory and history. And when the Shogunate came calling, looking for skilled samurai to fight the terrorist ronin in Kyoto, Kondo the humble teacher was anxious for an opportunity to use his skills in real life.


And as it turned out, Kondo Isami was very, very good at killing for real.


In the coming years, he would form what one historian called the most notorious band of killers in Japanese history.”


There’s actually a very rare photo of Kondo Isami taken towards the end of his young life, and when you look at it, you definitely get a sense of what an imposing physicality he had. Broad shoulders, square jaw, dark eyes. Actually, I’ll post that pic on the show’s Twitter and Instagram so you can see what I’m talking about. Because you look at it and instantly get the impression of a guy who will straight up murder you without hesitation.


One historian said Kondo was:


“a large, muscular man. His feet were so big that the maid employed at the home of a friend was “stunned by the unusually large size of his wooden clogs,” which he removed before entering the house


But Kondo also had a great sense of humor, and loved to joke around. He had one party trick that he loved to pull out at the bars in Kyoto:


His mouth was so big that he could fit his entire fist inside—an antic that drew hysterical laughter at drinking bouts.”


But when it came to his new gig, Kondo was all business.


He and a handful or other professional swordsman had been recruited by the Shogun for a very specific purpose. They were going to be the long arm of the Shogun’s justice in the lawless streets of Kyoto.


Their job was simple, hunt down and kill as many of the ronin terrorists that they could get their hands on. They had carte blanche to detain, interrogate, torture, maim, and kill without repercussions. They were the Shogun’s secret police, and they literally had a license to kill. It was called “kirisute gomen” or “license to cut down”.


The name of this very famous police force was the Shinsengumi. Which just means “Newly Selected Corps” in Japanese. But they were known by a different moniker on the streets of Kyoto. Their ferocity, brutality, and viciousness earned them the nickname “The Wolves”.


Now, you’d think that a secret police force would try and be as covert as possible. That they fly under the radar to avoid tipping off their targets. Well, the Wolves did exactly the opposite. If one of Kondo’s killers was walking down the street, you could instantly spot them.


Because the Wolves wore a very distinctive uniform. A flashy, sky-blue robe, with white zig-zags on the sleeves. As for Kondo, their commander,  his robe was marked with a distinctive skull insignia on the back. Very heavy metal. His wife had embroidered it for him as “a token of her appreciation for her warrior-husband’s resolve to die.”


The Wolves were very fashion-conscious. They even adopted a unique, intimidating hairstyle, according to Hillsborough:


“The men of the Shinsengumi tied their topknots into great clumps of hair. When they walked against the wind the bushy ends would flare out wider, evoking an even more imposing spectacle.”


The more you read about the Wolves, they start to sound less like a police force, and more like a street gang. They were technically law enforcement, but unlike law enforcement, the Wolves were answerable only to themselves. There was very little, if any, oversight from the Shogunate. The government just cut the checks and let Kondo and his men kinda do their own thing.


But that’s not to say the Wolves didn’t have any discipline. Quite the opposite, in fact. As commander of the Wolves, Kondo Isami implemented a series of extremely strict rules, which some historians refer to as the “Iron Code”.


The Iron Code had five rules.


  • Rule Number One – do not “raise money for selfish purposes”. In other words, do not abuse your position to make money on the side. The Wolves already got paid extremely well, so there was no excuse for any corrupt side hustles.


  • Rule Number Two – No “fighting for personal reasons”. So no personal vendettas. Your job is to kill ronin and terrorists, not pursue grudges or petty feuds.


  • Rule Number Three – No getting involved in litigation or legal disputes. So, I guess no jury duty. I don’t know that a weird one.


  • Rule Number Four – Never, ever abandon your position the Wolves. No going AWOL. Once you were in, it was for life, or until you died fighting. You don’t leave the Wolves. The Wolves leave you.


  • The fifth and final rule was extremely broad: No “Violating the code of the Samurai”. also known as Bushido.. This last rule basically boiled down to the expectation that, as a member of the Wolves, you were not allowed to show even the slightest whiff of cowardice or hesitation. There is no living to fight another day. If you get pinned down, you either kill your opponent or die in the process.


So that’s the Iron Code. But what would happen if you broke the Iron Code? Would you get a slap on the wrist? Maybe a fine? Or a demotion?


No. A violation of any of these rules was an instant, non-negotiable death sentence. You would be required to present yourself in front of the entire Wolfpack, express extreme contrition, reflect on your failures, then disembowel yourself with a dagger.


This is what I mean when I say the Wolves start to feel much more like a street gang than a police force. They had this unique internal culture. It almost a little reminiscent of something like the Hells Angels.


Well, Kondo, as I’ve mentioned, was a teacher at his core.


But he was a teacher who believed in hands-on experience. Experiential learning, if you will. He realized that if they were going to have a snowball’s chance in hell against this growing terrorist threat, they needed to be prepared for absolutely anything, all the time, 24/7.


According to Hillsborough:


To further prepare the rank and file for the myriad and unknown dangers of street fighting and actual warfare, special practice sessions were held in the dark of night, using real swords instead of the bamboo or wooden practice weapons of the training hall. Upon occasion the men were aroused from sleep by a fellow corpsman brandishing a drawn blade. The result could be bloody, if not fatal.


Kondo also believed that his pupils needed to know what it was like to actually kill someone before they could be expected to fight effectively.


“To hone their ability to cut through human flesh, the men of the Shinsengumi were subjected to performing executions, or serving as seconds for fellow corpsmen who had been condemned to commit seppuku.


After a few months of organization and training, they were ready. On August 18, 1863, Kondo and his Wolves hit the streets of Kyoto looking for blood.


They would find more than their fair share.  


--- ----- ---- MUSIC BREAK ---- ---- -----


In the early hours of June 5th, 1864, Kondo Isami was pacing nervously. He was running out of time.


It had been a year since he’d transformed a ragtag group of fencing students into the most feared killers in Kyoto. An elite counter-terrorism unit that everyone in the city recognized on sight, thanks to their flashy blue-and-white uniforms.


In that time, the Wolves had racked up a staggering body count. Kondo himself was known to have personally killed as many as 60 people. But unfortunately, there are some problems even a sword cannot solve.


And right now, Kondo’s most pressing problem, was the man hanging by his feet from the rafters in the other room. This man the Wolves had captured was a merchant named Kotaka Shuntaro. And he was a key conspirator in one of the most audacious terrorist plots the country had ever seen.


The plan was shocking, even to the battle-hardened Kondo.  


Hiding somewhere in Kyoto, was a cell of rogue samurai, or ronin. Their plan was to set fire to the city at a series of strategic chokepoints. And in the confusion, they would assassinate key members of the Shogun’s regime, and kidnap the Emperor of Kyoto, Japan’s living god. Their goal was to use the Emperor as a as a rallying point to bring others to their cause. Which would, in turn, trigger a final, devastating war against the Shogunate and its Western trade partners.


But despite having all these critical details, Kondo was missing a key puzzle piece of information. One he hoped to torture out of the traitorous shopkeeper. He needed to know “when”.


The shopkeeper, as it turned out, had an extremely high pain tolerance. Or a very deep devotion to his cause. Or both. The Wolves had been working on him for hours. The man was half-dead, but he still wouldn’t talk. Then, one of Kondo’s lieutenants has an idea. One last-ditch method of torture that just might break the man’s will to stay silent.


The lieutenant tells Kondo his idea. The commander listens, and approves. Do it, he says. So the lieutenant grabs two wooden rods. And he sharpens them into spikes. Then he takes a hammer and drives the wooden spikes through the shopkeeper’s bare feet.


Sounds bad enough, right?. Well the Lieutenant had a very creative build on this torture technique. He attaches a wax candle to each spike, and lights the wicks. The hot wax slowly drips down into the open wounds. This final excruciating torture was the breaking point for the shopkeeper. He begs them to stop. Please. I’ll tell you everything he se says. After that, the information starts pouring out. In a matter of minutes, Kondo had the critical piece of intel he needed.


As it turned out, the “when” of this terrorist plot imminent. Possible that every night.  But most importantly, the ringleaders of this this conspiracy would be rendezvousing that evening, on the other side of the city. At a place called the Ikedaya Inn.


Kondo knew he only had a few hours until the meeting was going to take place. And the conspirators had no idea that the Wolves had caught their scent. So Kondo gives the order for a strike team to prepare a raid on the inn.


As he sharpened his sword and pulled a shirt of chainmail over his skull pattern robe, Kondo must’ve been reflecting on the very long road that had brought he and his men to this climactic confrontation. Since he’d formed the Wolves, it had been a long year. One full of bloodshed, betrayal, and shattered alliances.




A year earlier, in 1863, Kondo and his elite band of swordsmen had hit the streets of Kyoto looking for trouble. Their mere presence was an open challenge to enemies of the Shogunate. By swaggering down the boulevards in their garish blue-and-white, with two swords on their hip, they were basically saying “anyone who’s got a problem with the Shogun, has a problem with us.”


The Wolves’ counter-terrorist operations tended to fall into two distinct categories. The first of which was targeted, special ops. As one contemporary described:


“Their surveillance at night brought them from rooftop to rooftop. If they discovered rōnin, they’d kick down the doors to arrest every last one of them, even thirty or forty at a time.”


The second kind of activity was the daily ritual of just walking down the street looking for trouble. Like beat cops. They would go on patrol, track down leads, gather information from spies and snitches, etc.


But the problem was, the ronin were out walking around too. Unlike modern insurgencies that rely on secrecy and prefer to keep a low-profile, the anti-Shogunate ronin were out in the open. In the bars, the hotels, the restaurants and the streets.


So when a Wolf and Ronin crossed paths while walking around town, it usually led to a good old-fashioned sword fight. These kinds of duels were very common, and very bloody. Again, it was a lot like gang warfare or turf disputes. But 9 times out of 10, the Wolves cut their opponents to shreds. Kondo had trained them very well, and everyone in the city was terrified of them. As one primary source recalled:


“The Wolves became the object of hatred among the ronin. They concluded that as long as Kondō and his men dominated the Kyōto scene, it would be difficult for them to effect an uprising.”


Kondo’s men killed ronin and anti-Shogunate sympathizers so often, that they turned their frequent bouts violence into a little game. They used to brag amongst themselves about how far they could get the blood of an enemy to spurt when they hacked off a head, a limb, or a hand. As one contemporary remembered:


Every day the men would go out and cross swords with the enemy. One corpsman claimed that the blood of the man he had killed today splattered on the ridge of the adjacent house. Another boasted that the blood of the man he had cut down had reached the roof of the house.


The Wolves and their excessively violent methods began to alarm local authorities. At first, the Wolves had been a godsend. Like exterminators taking care of an infestation.

But now, the Wolves were getting out of control. They became increasingly arrogant and aggressive. Before long, they weren’t just killing ronin, they’d cut down anyone one who looked at them the wrong way.


As Kondo Isami himself admitted: “We killed anyone who insulted us”.


Their reputation grew and grew to almost mythic proportions in Kyoto. As one witness to a raid remembered:


“They searched the entire house most violently. I was frightened because during those days the Wolves derived pleasure from killing people. While I was shaking with fear, a person who seemed like the commander came and quieted everyone down...  That was the first time I ever saw Kondō.”


The Wolves used their fearsome reputation and generous pay from the Shogun to live like kings in the city. As one contemporary source observed:


“They had no shortage of money... . No matter where they went, they were well received by the women.”


Some Shogunate officials began to worry they had just swapped one group of violent thugs for another. And the most violent Wolf of all, was a man named Serizawa Kamo.


Before he had joined the wolves, Serizawa had been a criminal, rotting in a jail cell.


Like Kondo, Serizawa was a swordsman by trade. But whereas Kondo was fairly principled and stoic, Serizawa was erratic, violent, and cruel. Before the Shogunate had put the word out that it was looking for samurai to defend its interests in Kyoto, Serizawa had been sitting on death row.


He’d been condemned to be die for mutilating and murdering three men over a petty disagreement. It wasn’t his first brush with the law either. As a teenager, he’d raped several maids who cleaned his family’s house.


But regardless of his bad reputation, the Shogun needed soldiers, and Serizawa was granted amnesty and pardoned, on the condition that he would serve the Shogunate in the newly formed counter-terrorist task force. He had to become a wolf, or die. Serizawa agreed.


Kondo did not like Serizawa. And Serizawa did not like Kondo. But they were the most experienced men in the unit, so these two polar opposites found themselves working together in service of a larger goal.


Kondo knew that this guy was bad news. But the Shogunate had, for better or worse, selected this wildcard for the Wolves. There was nothing the commander could do. But Kondo’s instincts were spot-on. Serizawa was not the kind of man you give a license to kill to.


Serizawa the ex-con was a deeply hateful, vindictive person, and it didn’t help that he also had a huge drinking problem. He was “a pathological drinker” according to one source, which made him all the more dangerous to the residents of Kyoto. In the early months of the Wolves existence, Serizawa achieved a terrifying notoriety that hung over the Wolves like a noxious cloud.


It was said that Serizawa once passed a dog that was begging for scraps of food on the streets. On a whim, he struck it on the head with a heavy iron fan, killing it instantly.


On another occasion, a zoo had come to Kyoto. One of the exotic animals displayed was a tiger. Well, Serizawa wandered in drunk one day, and asked if the tiger was real, or just some other animal painted to look like a tiger. They assured him it was real. Well before anyone could register what was happening, Serizawa drew his sword, and stuck it into the cage, stabbing the tiger. When the animal roared aand hissed, Serizawa laughed and said “It’s a real tiger.”


But Serizawa’s casual cruelty wasn’t just limited to animals. One day, a doctor diagnosed him with syphilis. He became convinced that he had contracted the disease from a certain geisha. So he marched down to the teahouse where she worked, and cut her in half with his sword. Then he kicked her body into the river.


On another occasion, Serizawa and some of his fellow Wolves were drinking sake in a brothel. He asked two of the serving girls to sleep with him, but both said ‘no thanks’. The next day, he returned to the brothel and cornered the owner, saying:


“Their insult to a samurai was inexcusable. I should kill both of them for their insult. But since they’re women, I’m going to pardon them. Instead, I’ll cut their hair.”


He drew his short sword and cut off both of the women’s long black hair. His intention being to rob them of the beauty that he had coveted and been denied.


The dynamic between Kondo the teacher and Serizawa the ex-con was an interesting one. Neither liked the other, but they had to work together in this uneasy professional bond.


It’s funny, but you know what it actually reminds me of? Robert DeNiro and Joe Pesci in any Scorcese mob movie. The personality traits and the way they play off one another ar every similar.


Kondo is very much like DeNiro. Stern, stoic, dangerous, but reasonable.


But Serizawa is like Joe Pesci. Unpredictable. Erratic. Capable of sudden, shocking violence at the drop of a hat. Over the slightest provocation.


It wasn’t long before Kondo started getting tired of cleaning up Serizawa’s many messes. As one of the rank-and-file Wolves remembered: “his extreme violence perplexed even us.”


Occasionally, Serizawa’s aggression could draw the entire force into a feud. For example, one day, Serizawa was crossing a narrow bridge near Kyoto. It was really hot outside, so the swordsman was only wearing a thin, loose robe, rather than the distinctive blue-and-white Wolf uniform.


As he’s crossing this bridge, Serizawa’s way is blocked by this giant of a man. Huge belly. Massive arms. Serizawa immediately realized that this guy was a Sumo wrestler. Serizawa, annoyed at the delay, says “Move to the side”. But the Sumo wrestler just stayed put. He gives Serizawa a defiant, mad-dog glare, as if to say, No, you move.   


Before the wrestler can even blink, Serizawa draws his sword and in a single motion, slices open the man’s belly. The big man dropped like a stone, bled out and died twitching right there on the bridge.


Later that night, Serizawa and some of his Wolf buddies were drinking at a bar. Suddenly, they hear a commotion outside, so they go to investigate. They find twenty huge sumo wrestlers waiting for them in front of the bar, each armed with a heavy wooden club. The man Serizawa had killed earlier that day was a member of their wrestling club, and they wanted revenge.


The problem was, the wrestlers didn’t realize they were challenging the Shogun’s secret police to a fight. Serizawa and his boys weren’t wearing their uniforms. But rather than de-escalate, the Wolves draw their weapons and charge these huge wrestlers, “brandishing their swords like windmills.”


Within a few minutes, five of these giant Sumo wrestlers were in pieces on the street. And the other 15 were running for their lives. The Wolves informed the local magistrate of the incident, with a warning:  


“Be informed in advance. that if they should attack us again, we will kill every last one of them.”


The magistrate agreed, and certainly didn’t want to piss off the Shogun’s notorious secret police. So, he issued a verdict on the matter:


The samurai whom the wrestlers attacked were men of the Shinsengumi. There can be no greater insult than starting a fight with samurai. It was perfectly reasonable for those samurai to seek retribution for such an insult.”


The wrestlers were obliged to smooth the feud over with a barrel of sake, a bribe, and a profuse apology. Clearly, the Wolves were borderline untouchable from a legal perspective, and they knew it.


But Serizawa and his violent antics were exhausting Kondo’s patience. This guy was a rabid dog, and sooner or later, he would need to be put down.


As one Wolf remembered: “Serizawa became more and more agitated. He now engaged in misconduct day and night according to his whims and without any regard for the corps.”


The final straw came in early 1864, when it was discovered that Serizawa had been abusing his authority and extorting local businesses for money as part of a protection racket. As he told the business owners: “Law and order are not free of charge.”


This was in direct violation of the Iron Code. And if that wasn’t bad enough, when one of the businesses refused to pay up, Serizawa set the building on fire. The Shogunate was furious. They were paying the wolves to keep the peace, not intimidate and extort local businesses. It was clear: Serizawa had outlived his usefulness.


Kondo was quietly informed that he had the green light to assassinate this problematic Wolf. Kondo was obviously no fan of Serizawa, so he happily organized the hit.


One night, a handful of Wolves took Serizawa out drinking. They pour sake bottle after sake bottle into this guy. Once they’re confident that he’s too inebriated to defend himself properly, they wait for him to pass out in a room upstairs. Then they stab him to death while he’s sleeping, along with the mistress lying next to him.


With Serizawa’s death, Kondo had eliminated his key rival and acquired full control over the Wolves in one fell swoop. But he would not have long to bask in this windfall.


He and his men were about to face their greatest challenge yet. A fateful showdown with the terrorist ronin at a place called the Ikedaya Inn.


--- ---- MUSIC BREAK --- ---


On the evening of June 5th, 1846 – that pivotal night we’ve been returning to throughout the episode -  the city of Kyoto was buzzing with activity. It was the eve of the famous Gion Festival and the residents of Kyoto were out celebrating. As Romulus Hillsborough poetically described the atmosphere:


Red and white paper lanterns lit both sides of the main road, glowing in front of the various shops, teahouses and restaurants. The steady pounding of drums, the winding of flutes, and the continuous clanging of brass bells filled the heavy, humid air. As nightfall offered no relief from the intense heat and humidity of the day, throngs of people filled the streets.”


Kondo Isami and his wolves had no time to celebrate. Somewhere in the city, a group of ronin were meeting, finalizing the details of a plot to burn the city to the ground and kidnap the Emperor of Japan.


After torturing the conspiratorial shopkeeper with a pair wooden spikes and some scalding candle wax, Kondo had finally squeezed out the last key piece of information he needed. This terrorist cell was meeting that night, at 5’oclock, at well-known establishment called the Ikedaya Inn.


So Kondo strapped his two swords to his waist, pulled on a shirt of chain mail, and donned a simple iron helmet. He selected a handful of his best swordsman for a small, 10-man strike team. He knew they’d be outnumbered; the shopkeeper had estimated upwards of 20 ronin would be at the Ikedaya that night. But Kondo was confident. The terrorists had no idea that the Wolves had caught their scent. They had the element of surprise.


Across the city, the ronin were starting to gather for their meeting at the Ikedaya. The Inn was a two-story establishment, and the serving girls went up and down the stairs, bringing bottle after bottle of sake as the conspirators discussed and finalized the details of their plans.


A few of them however, were getting a little nervous. Something was wrong. Their contact who had agreed to supply guns and weapons for the attack, a certain shopkeeper, had gone missing. He hadn’t shown up for their rendezvous. And no one could find him. Little did they know, the shopkeeper was already dead, hanging upside down with spikes through his feet from the rafters of Shinsengumi HQ.


At around 10 o’clock PM, the owner of the Ikedaya Inn hears a knock at the front door. “Who’s there?” he asks. No answer. The innkeeper slides open the door to find Kondo Isami, commander of the Wolves. In full battle gear, flanked by 9 other heavily armed men. Kondo says:


“We’re the Shinsengumi. We’ve come to search the place.”


The innkeeper knew who Kondo was. He knew the Wolves, and their reputation, and what they would do to him if they discovered his guests upstairs. The innkeeper panics and runs for his life.


Kondo and his men storm the Ikedaya Inn, pushing through the fragile sliding doors. Kondo commands five of his men to cover the exits so no one can escape. Then he and four of his Wolves file up the steps to the second story. They enter the room and see twenty very drunk ronin glaring back at them.  


Kondo cleared his throat and addressed the room:


“We’ve come to investigate. If you resist, we’ll kill you without mercy.”


For the first few moments, no one moves. One of the ronin suddenly draws his sword and rushes Kondo and his men, shrieking. One of the Wolves steps forward and kills the man with a single, fluid motion. The attacker was dead before he hit the ground.


Upon seeing the death of their friend and comrade, the ronin make their move. As one of Kondo’s men remembered, “they came at us like cornered rats”.


It’s very hard to verbally choreograph as sword fight between 30 people, in a two-story hotel, in the middle of the night. Odds are, the visual that pops into your head, is more interesting than anything I could conjure up. But long story short, the Wolves spend the next two hours butchering these drunk ronin.


When you think of samurai fighting each other, the mind tends to go right to an Akira Kurosawa flick. Something cinematic, and graceful. The empty street, the snow gently falling on composed, respectful combatants. It’s almost like a dance.


Well this showdown between the Wolves and the terrorist ronin was not a dance. It was more like a UFC fight with swords. There’s screaming, and slashing, and biting, and wrestling. Blood is literally flying everywhere. They were swinging their swords at each other so hard that Kondo later said: “sparks flew from the blades”.


An eyewitness to the battle described what was left of the Inn when the fighting finally ended:

“Not one of the paper screen doors was left intact, all of them having been smashed to pieces. The wooden boards of the ceiling were also torn apart when men who had been hiding above the boards were stabbed with spears from below. The tatami mats in a number of rooms, both upstairs and downstairs, were spotted with fresh blood. Particularly pitiful were the arms and feet, and pieces of facial skin with the hair still attached, scattered about.”


When it was all said and done, 11 terrorist ronin were dead and 23 were captured. Several of them had committed suicide in the street rather than be taken alive. The innkeeper was later apprehended and died “due to severe torture” by the Wolves.


Only three members of the Wolves had lost their lives. But it was a hard, desperate fight, even for expert killers like the Shinsengumi. As Kondo admitted:


“I have been in frequent battles ... our opponents were many and all courageous fighters, so that I nearly lost my life.”


As the sun rose on Kyoto the next morning, Kondo and his men marched back to their headquarters throughout the city. One of the men remembered: “a crowd of tens of thousands [watched us] from the roadside.” The Wolves swords were so dented and bent from the two-hour brawl that they couldn’t even put them back in their scabbards.


And the hero of the hour was their commander, Kondo Isami. According to someone who spoke with him hours after the slaughter at the Ikedaya Inn, Kondo was:


“so composed, that one would never have thought he had just fought such a fierce battle.”


In Kyoto, the Wolves were considered heroes. In a single night, they had narrowly foiled an act of terrorism that could’ve destroyed the imperial city, and destabilized all of Japan.


After the Ikedaya Inn, every swordsman worth his salt wanted to be a member of the Shinsengumi. The Wolves are flooded with new recruits, would-be warriors who wanted to fight and die under the command of the famous Kondo Isami. The size of the Shinsengumi increased significantly in the wake of the Ikedaya Incident.


The other thing that swelled, was Kondo’s arrogance and self-importance. He had come a long way from being a nobody fencing instructor. His name was known throughout the entire country. And that celebrity led to what one of his men called: “reckless ... and egotistic behavior.”


The humble teacher had transformed into a petulant rock star. A bona fide celebrity who had the power to kill at will, and often did.  As one Wolf observed bitterly: “He treated our comrades at headquarters as if they were his vassals. If they did not listen to him, he would resort to the sword.”


Many of the older Wolves, repelled by this new change in their leader, wanted to leave the force. But they could not. According to the Iron Code, that was capital offense, punishable by ritual suicide. So most of them had to shut up and tolerate the imperious commander that they had once held in such high esteem.


But for Kondo, fame was a double-edged sword. After hearing that their comrades had been butchered by the Wolves at the Ikedaya, the thousands extremist ronin and anti-Shogunate clans throughout the country were outraged. They had been too cautious, they decided. Too covert. Maybe striking from the shadows was the wrong strategy. Ironically, the Ikedaya Incident did not discourage revolution, it only inflamed it.


Over the next several years, the tide of anti-Shogunate sentiment continues to rise. No matter how many plots they foiled, or people they tortured, or ronin they killed, the Wolves and their masters in Kyoto could not stamp out the embers of change.


Anyone with a brain could see - - a ground shaking ideological shift was happening. The Shogun’s time was over. It was becoming clearer every day: The old order had to die, along with everyone who defended it.


This contagion of political dissent was so widespread, it even wormed its way into the ranks of Kondo’s killers. Even they were seduced by the idea of a fresh start for the country, led by the Emperor of Japan, rather than the Shogun they had sworn to fight for.


But Kondo was like a rock. He didn’t care that that the Shogunate was weak. He didn’t care that his enemies were multiplying every day. He didn’t care that the ronin had placed a price on his head. He was a ride-or-die supporter of the Shogun. After all, he thought, only through the Shogunate had he been transformed from a lowly teacher to a powerful commander of men. The Shogun had made him wealthy and powerful. He owed everything to him.. By that logic, He was honor-bound to continue supporting the Shogunate, no matter what happened.


Well, not all the Wolves felt that way. The Iron Code was clear about what happened to deserters and defectors. But several of the Wolves decide to leave the Shinsengumi. Genuinely moved and inspired by the revolutionary fervor raging across the country, they make a run for it.


For Kondo, this was unacceptable. If the Iron Code could be broken without consequence, then the Wolves were no more than street gang. No one leaves the Wolves.


Kondo mercilessly hunts down these men who try and leave the Shinsengumi. No matter how far they ran, he sent men to cut them down and bring back their heads as proof. But even that failed to satisfy the commander’s growing paranoia. Before long, he began preemptively killing anyone he suspected of harboring revolutionary sympathies within his organization.


As the country was collapsing around them, the Wolves were collapsing in on themselves.


In 1868, four years after the great victory at the Ikedaya Inn, the simmering tensions between the supporters of the Shogun and supporters of the Emperor, erupts into an all-out civil war. A massive army is formed in opposition to the Shogun, consisting of a coalition of Western clans that were intent on seeing the current military government toppled, and the Emperor raised to his rightful place as ruler of the country.


As this army advanced and eventually overtook the city of Kyoto, Kondo and the wolves, along with the rest of the pro-Shogunate forces, were forced to flee. They had to retreat in shame from the streets they gad once ruled with an iron fist. A few short years after the Ikedaya Incident, Kondo and his killers were on the run.


As the Imperial Forces drove the Shogun’s armies further and further back, Kondo could feel the noose tightening. There were fewer safe places with each passing day. At this point, his celebrity status was no longer a badge of honor, it was a liability. So he assumes an alias to move safely along the roads and through villages, avoiding his enemies.


One night, Kondo and a few of his men were riding on horseback to meet with some of their allies from the Shogunate. Out of the dark, muskets suddenly blazed and peppered the group with bullets. Kondo was hit in the shoulder and started bleeding heavily. The ambushers rushed the riders, pulling two of the men off their horses and stabbing them with spears and swords. Kondo managed to gallop to safety despite his wound, barely escaping the trap.


He later learned who had organized the ambush. It wasn’t the extremist ronin, or the anti-Shogunate clans. It was former men of the Shinsengumi who had tried to kill him. Ex-Wolves who were angry at having watched their friends die in Kondo’s paranoid purges. The commander of the Wolves, once all powerful, now realized he had very few people he could trust.


Kondo’s luck evaporated completely a few weeks after that.


He and a handful of loyal wolves had been hiding out in a Miso factory outside of the capital, when their safehouse was stormed by revolutionary forces. To their shock and surprise, Kondo surrendered, rather than fight to the death. As he was led away in shackles, he must’ve recognized the irony. Not so long ago, he had been the one raiding safehouses and apprehending terrorist ronin in Kyoto. In a painful twist of fate, Kondo Isami had become the outlaw.


Initially, the revolutionary forces didn’t realize who they had captured. They thought  they’d just apprehended another Shogunate sympathizer. But as Kondo is led back into their camp as a prisoner, someone recognizes him. A former Wolf, who Kondo had driven away in his bloodthirsty purges, raises his finger and points. That, he says, is Kondo Isami. Commander of the Wolves.


A hasty trial is organized and conducted, and after a very, very short period of deliberation, Kondo is sentenced to death for his quote-unquote crimes in Kyoto. As the prosecution described him:


He was a crafty scoundrel who committed evil for many years and killed a countless number of our men. But now he’s been arrested and will die... . The old fox has deceived people. But it’s one of the funniest stories ever that the old fox came out during the daytime to be caught so easily. The notorious Kondō Isami arrested without a fight—now all the other foxes will certainly perish.


But not everyone at this trial hated Kondo. Many could not help but feel a grudging respect. One man was particularly moved by the death sentence of this famous samurai:


I simply watched the tragic scene, all the while wondering if this is what happens when one loses a war. I was overcome by sympathy; tears flowed down my cheeks. Kondō wore an intensely grievous face as he looked at me.


On May 17th, 1868, Kondo woke up and prepared to die. It was common for samurai who were facing death to compose a poem or a verse to commemorate their own life. This is what Kondo wrote just hours before his death:


Submitting to the will of another, I have nothing to say on this day. I value honor above life. Ah, the long flashing sword to which I readily surrender, and repay my lord’s kindness with my life.


Normally, a samurai in Kondo’s position would be allowed to commit ritual suicide. A way of dying with dignity. Well, these revolutionaries and ronin did not want to give him that courtesy. To them, he was a thug, a gang leader, and a killer. They decided that Kondo would be executed like a common criminal.


They did allow him one small courtesy. Kondo knew that his head would be displayed publicly as a warning to all those still supporting the Shogun. So he asked if he could at least shave his face before they took his head. They agreed. But the executioner shaved his face for him; they still were afraid to give the Commander of the Wolves an edged weapon. Even a 2-inch razor.


As a sword hovered above his neck, Kondo said his last words.


“I have been a great trouble”


With that, he held up his topknot so that the executioner could get a clear cut at the base of his neck.


One witness to execution could only remember the moments before the fateful cut, and nothing after.. They recalled: “There was a flash” and then Kondo Isami’s head fell into a pit that had been dug in the ground to catch the gushing blood. He was 34 years old.


Another witness to Kondo’s execution said:


His countenance was the same as always in the face of death, and he died with composure. Those watching shed tears of sorrow for Kondō. He was truly a great man, unequaled throughout the ages.”


This episode was slightly unique in that it focused on a very narrow viewpoint, in a very large event. Kondo and Wolves were just one of hundreds of individual factions navigating this incredibly complex time in Japanese history. It was a period of radical change and constant realignment.


The arrival of Commodore Matthew Perry to Japan in 1853 changed the country forever. But the way Japan responded to the influence of Western powers was singular, and followed a remarkably different trajectory than that of China, Southeast Asia, or India.


Eventually the Japanese Civil War ended, and the Shogunate was destroyed after 250 years of supremacy. In the decades that followed, Japan modernized shockingly fast, a transformation that’s become known as the Meiji Restoration.


This is one of those periods that if you’re into, you’re *really* into. Which, admittedly, I am. I have a huge soft spot for Japanese history. And my intention is to periodically return to the Meiji Restoration era and tell the story from a few different angles.


Because although the story of Kondo, the wolves, and the Ikedaya Inn is fascinating in its own right, there was a lot going on in the country at the time. And we’ve only scratched the surface here. But for now, I hope you enjoyed this look at an underappreciated corner of history.


This has been Conflicted. Thanks for listening.



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